Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 52, Pages 18742-18746Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201604999
Keywords
asymmetrical synthesis; bioorganic chemistry; chemoenzymatic synthesis; glycosylation; N-glycans
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Funding
- National Institute of General Medical Sciences from the U.S. National Institutes of Health [R01GM090269, P01GM107012]
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A divergent chemoenzymaytic approach for the preparation of core-fucosylated and core-unmodified asymmetrical N-glycans from a common advances precursor is described. An undecasaccharide was synthesized by sequential chemical glycosylations of an orthogonally protected core fucosylated hexasaccharide that is common to all mammalian core fucosylated N-glycans. Antennae-selective enzymatic extension of the undecasaccharide using a panel of glycosyl transferases afforded core fucosylated asymmetrical triantennary N-glycan isomers, which are potential biomarkers for breast cancer. A unique aspect of our approach is that a fucosidase (FucA1) has been identified that selectively can cleave a core-fucoside without affecting the fucoside of a sialyl LewisX epitope to give easy access to core-unmodified compounds.
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